Plymouth Vacation Packages

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Your Plymouth Vacation

With plenty of highlights as well as some hidden gems, this city is best experienced with a Plymouth vacation package. Look for places to stay in Litchfield Historic District, which is great for shopping, dining and history. If sightseeing is on the agenda during your trip to Plymouth, check out popular attractions like Black Rock State Park. Stop daydreaming and start traveling. Browse the range of options on Expedia today and put your Plymouth vacation plans into action!

Top Plymouth Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2 out of 5
Price was CA $640, price is now CA $635 per person
CA $635
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New Haven (HVN)
7.2/10 Good! (483 reviews)
I'm elderly person this was the greatest hotel I ever been there everything was excellent the breakfast was amazing housekeeper kept my room immaculate I enjoyed my stay I love feeding the ducks on the ponds I have a disease I'm allergic to the sun I love the gazebo it was so refreshing at night to see sunrises and sunsets I do plan to come here all the time it deserves a five star the people they hired are very professional keep it up

Reviewed on Jul 22, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,058, price is now CA $1,654 per person
CA $1,654
per person
Sep 7 - Sep 10
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
No reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $815, price is now CA $691 per person
CA $691
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New Haven (HVN)
8/10 Very good! (1,000 reviews)
Staff was friendly. Room was unappealing. Upholstered furniture was so covered with stains, we would not be comfortable sitting on or placing any belongings on the chairs. Bathroom outdated, but relatively clean. Would not stay here again or recommend it.

Reviewed on Jul 24, 2026

Head of Pond House

Head of Pond House

3 out of 5
Price was CA $1,457, price is now CA $1,369 per person
CA $1,369
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
10/10 Exceptional! (8 reviews)
I don’t even know where to begin with this place. It’s heaven. The house is beautiful, situated right next to the lake with a serene backyard and dock you can go sit on. The rooms are beautifully decorated and spacious, and feel understatedly luxurious. Pauline was an incredible host, welcoming us from the moment we got in with recommendations and a tour of the property. Breakfast was healthy and delicious each day, and there was a fridge with beverages and snacks you could help yourself to at any time. It was a perfect getaway and I can’t wait to come back.

Reviewed on Jul 19, 2026

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
Price was CA $1,694, price is now CA $1,682 per person
CA $1,682
per person
Aug 27 - Aug 30
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.6/10 Exceptional! (1,012 reviews)

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Plymouth Hotel Deals

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
The price is CA $133 per night from Aug 9 to Aug 10
CA $133
CA $153 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,387 reviews)
"The bed was extremely comfortable but the pillows weren’t. The property was clean and pretty well maintained. We were there for the little league softball regionals in Bristol so the location was good only about 15 min from the complex. Price was excellent compared to all others."

Reviewed on Jul 24, 2026

Holiday Inn Express Southington by IHG
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Aug 17 to Aug 18
CA $130
CA $150 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very good! (1,262 reviews)
"Great experience"

Reviewed on Jul 24, 2026

Wyndham Southbury
Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

2.5 out of 5
2260 Whitney Ave Hamden CT
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Aug 10 to Aug 11
CA $152
CA $175 total
Aug 10 - Aug 11
includes taxes & fees
Hamden Hotel and Suites – Hamden New Haven
See all 698 properties in Plymouth
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

How much does a Plymouth vacation package cost?
You'll find cheap prices from CA $635 on Expedia for your Plymouth break. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Plymouth costs.
What are the cheapest months to go to Plymouth?
You're likely to find reduced prices and greater availability in January, February and March. Check out our cheap Plymouth vacation packages and you could get some great off-season discounts.
How many days is enough for Plymouth?
The ideal length of your Plymouth vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you plenty of time to hit all the main sights and discover some hidden gems along the way.
How to find the best Plymouth package deals?
Use Expedia's filter tool to help you find some of the best Plymouth package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Plymouth package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Plymouth vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still have the freedom to create a customized Plymouth vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Plymouth?
If you're planning a spur-of-the-moment Plymouth trip, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Plymouth?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred season and the type of activities available will also help you decide when to escape to Plymouth.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to experiences and flights. Your accommodations will likely be the biggest expense during your trip to Plymouth.
  3. Decide how long to go away for: Now that you're more familiar with Plymouth, you can work out the ideal length of your break. Pull together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Plymouth vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.